Filifolide A

Details

• Internal ID: f2340931-ad77-40c7-951a-1739fdef5534
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,5S)-2,2,4-trimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-one
• SMILES (Canonical): CC1=CC(C2CC1OC2=O)(C)C
• SMILES (Isomeric): CC1=CC([C@H]2C[C@@H]1OC2=O)(C)C
• InChI: InChI=1S/C10H14O2/c1-6-5-10(2,3)7-4-8(6)12-9(7)11/h5,7-8H,4H2,1-3H3/t7-,8-/m0/s1
• InChI Key: JHKNAYGQYUKKDQ-YUMQZZPRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22 g/mol
• Exact Mass: 166.099379685 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 50585-61-0
• DTXSID901345698
• Q63409043

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	-	0.5958	59.58%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5865	58.65%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9294	92.94%
P-glycoprotein inhibitior	-	0.9546	95.46%
P-glycoprotein substrate	-	0.9318	93.18%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9377	93.77%
CYP2C9 inhibition	-	0.9395	93.95%
CYP2C19 inhibition	-	0.7354	73.54%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8128	81.28%
CYP2C8 inhibition	-	0.9821	98.21%
CYP inhibitory promiscuity	-	0.8098	80.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8636	86.36%
Carcinogenicity (trinary)	Non-required	0.5161	51.61%
Eye corrosion	-	0.8746	87.46%
Eye irritation	+	0.9121	91.21%
Skin irritation	+	0.6071	60.71%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5897	58.97%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	+	0.7964	79.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	+	0.7822	78.22%
Acute Oral Toxicity (c)	III	0.7441	74.41%
Estrogen receptor binding	-	0.8142	81.42%
Androgen receptor binding	-	0.7598	75.98%
Thyroid receptor binding	-	0.8127	81.27%
Glucocorticoid receptor binding	-	0.9140	91.40%
Aromatase binding	-	0.8821	88.21%
PPAR gamma	-	0.7991	79.91%
Honey bee toxicity	-	0.8003	80.03%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8482	84.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.75%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.06%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.83%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.89%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.42%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.52%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	83.39%	89.63%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.55%	86.00%
CHEMBL1871	P10275	Androgen Receptor	81.79%	96.43%

Plants that contains it

• Achillea ligustica
• Artemisia filifolia
• Conioselinum smithii
• Seriphidium deserti
• Volutaria tubuliflora

Cross-Links

• PubChem: 90472998
• NPASS: NPC277974
• LOTUS: LTS0075324
• wikiData: Q63409043